53 Flag Hill Road
Colebrook, Connecticut 06021
- Beds
- 0
- Baths
- 0
- SqFt
- —
- Acres
- 27.21
- Property Type
- Land

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Discover an exceptional opportunity to create your own private country estate on 27 beautiful acres in the charming Litchfield Hills. Bordering protected Land Trust property an backed by a wildlife preserve, this remarkable parcel offers an extraordinary sense of seclusion, privacy, and connection to nature-yet provides the flexibility to bring your vision to life. Located at the end of a cul-de-sac, the property features a natural, regular configuration with a picturesque stream meandering east to west through the center of the land. Approximately two acres of cleared, buildable area provide an ideal setting for your dream home, while an existing 350 feet of finished driveway leads toward the homesite, with an additional 350 feet of roughed-in driveway already in place. With its open land, wooded acreage, natural water feature, and exceptional privacy, the property is ideally suited for a private estate or horse farm. There is also potential for subdivision and development, offering an attractive opportunity for those seeking both long-term flexibility and investment potential. The property is designated **PA 490 Forest Land**, providing a valuable property-tax reduction. A septic and soil test, property survey, and wetlands survey covering the first third of the property are on file. This extraordinary 27-acre parcel offers the rare combination of privacy, natural beauty, infrastructure, and potential that is increasingly difficult to find in the Litchfield Hills.
Key Facts
- City/Town
- Colebrook
- Neighborhood
- N/A
- Property Type
- Land
- Days on Market
- 0 days
- Beds
- 0
- Baths
- 0 baths
- Lot Size
- 27.21 acres
- Property Taxes
- $921 / Annually
Market Snapshot
The Colebrook Market
Land · trailing 12 months
Active Listings
6
Colebrook inventory
Median List Price
$522,500
6 active listings
Median Closed Price
$40,000
3 sales
Median Days on Market
212
6 active listings
Median $ / Sq Ft
--
6 active listings
Sale-to-List Ratio
80.2%
3 sales
How this home compares
List Price
$269,900
vs $522,500 median
48.3% below median
Price / Sq Ft
--
Median unavailable
Limited comparable data
Days on Market
0 days
vs 212 days median
212 days fresher than median
Based on 6 active and 3 closed sales (trailing 12 mo) of land in Colebrook. Source: SmartMLS · As of August 29, 2026.
Location
53 Flag Hill Road, Colebrook, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$1,388
- Property Taxes$77
- Insurance$90
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Colebrook
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Land
- Subtype
- SingleFamilyResidence
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Exterior & Lot
- Lot Size
- 27.21 acres
- Zoning
- R2
- Waterfront Details
- Not Applicable
- Water Source
- Well Required
- Sewer
- Septic Required
- Flood Zone
- No
- Lot Description
- SecludedAdditional Land Avail.On Cul-De-SacRolling
Listing & Financials
- Property Taxes
- $921 / Annually
- Days on Market
- 0
- MLS #
- 24202868
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 8/29/2026 at 11:31 PM UTC.